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Over the last two decades, the impact of community characteristics on the physical and mental health of residents has emerged as an important frontier of research in population health and health disparities. However, the development and evaluation of measures to capture community characteristics is still at a relatively early stage. The purpose of this work was to assess the reliability of a neighborhood audit instrument administered in the city of Chicago using Google Street View by comparing these “virtual” data to those obtained from an identical instrument administered “in-person”. We find that a virtual audit instrument can provide reliable indicators of recreational facilities, the local food environment, and general land use. However, caution should be exercised when trying to gather more finely detailed observations. Using the internet to conduct a neighborhood audit has the potential to significantly reduce the costs of collecting data objectively and unobtrusively.